We can accommodate up to 6 passengers on each voyage to ensure a comfortable and personalized experience for all guests. However, if six seats are booked guests are allowed to bring two more, no more than 8.

Seats are priced at $120 for our 2-hour voyages and $135 for the Sandy Toes Beach Voyage.

It is up to your captain to decide. Please wear appropriate clothing during the winter months. There are blankets and throws available on your boat! (Obviously we are not going out in pouring rain or lightening). If you purchased travel insurance through our booking system there will be 100% refund due to weather cancellation.

YES!! Absolutely! We have an onboard YETI Ice Chest with additional wine coolers for opened bottles. We have ice and barware available. Please drink responsibly. The captain may have a special reserve hidden away if you ask.

Yes and Yes. We have clean custom barware available with clean ice.

On the sunset voyage there will be a light fruit and cheese platter included.

Guests are encouraged to bring their own cigars and repeat guests leave some cigars aboard. (There are limited spaces in the "Captain's Humidor.") Each guest will have at least one cigar available from a curated sampler.

Yes and Yes. Both V and Flat cut available.

No, there isn’t a restroom on board. However, we can dock at nearby locations with restrooms within 5-10 minutes. Simply let the captain know, and we’ll accommodate your request. If sharing the boat, please be mindful of other guests.

Cancellations made within 48 hours are fully refundable. Beyond this period, the full fee is non-refundable. We uphold this policy to ensure reliability and maintain our high standards.

NO, you will forfeit your full amount if cancelling less than 48 hours before your voyage. We expect a synergistic relationship with our Customers and Services Provided. We may not be the right fit for everyone; we completely understand if you need more flexibility. There are other local tour operators that maybe a better fit.

No, you only receive refund when cancelling within 48 hours.

Yes, your assigned captain is aware of this option and will cater to your groups wishes. If you have experience cruising with us, you can request the themes that you like best, or a blend of some or all themes.

Yes, please reach out to us and we can schedule a fully customizable experience.

Yes, please reach out to us and we can schedule a fully customizable experience.

Yes, our voyages operate every day even on holidays

Yes, If your party requires advanced booking outside our 7 days booking window please reach out and we can schedule accordingly. Due to the high demand volume, we require a 50% non-refundable deposit for advanced bookings. The deposit is only refundable if voyage is cancelled due to weather or mechanical issues.

Our booking availability window is one month out. Please contact our concierge for advanced booking inquiries.

We say 5-7 days. However, it depends on your bank. Sometimes, if you book and cancel the same day, the refund is usually issued the same day. Other times, it may take 1 day or 2 days. We use 5-7 as a standard average.

Only if you book all 6 seats. If you are sharing the boat with other guests, we must stay with the selected theme. Again, with a private voyage, you and your captain can design the outing however you’d like.

Yes, many customer’s take and UBER to the dock to capitalize on this luxury. Your captain may drop you off at any restaurant or shopping area in Naples Bay you would like. Please be courteous of other guests if this is not a private tour. We don’t want to disrupt other’s experience. Some customers are dropped off at a different location than pickup and simply take an UBER back to their cars later.

You will receive no refund as you have reserved a seat that could have been claimed by another guest. Feel free to refer to our cancellation policy. Cancelling within 48 hours is totally acceptable.

Totally fine, the boat comes back at the same time regardless of what time you leave.

Yes, any timeslot that you have booked for a private charter you can choose the theme for your guests. Just let your assigned captain know that you are a private VIP and let him know your preferences. As always, there will be a Yeti cooler with Ice aboard daily. You can bring your own drinks on any of the cruises.

Yes, please reach out to us and we can schedule a fully customizable experience

Yes, please reach out to us and we can schedule a fully customizable experience.

Yes, our voyages operate every day even on holidays

Yes, please reach out to us and we can schedule a fully customizable experience

You will be assigned a captain at checkout and will be notified who your assigned captain is via email and text once you checkout. There are no guarantees and no way to request a particular captain as there are others requesting captains as well. The most likely way to do it is to have an advanced private booking. This will give admin the time to schedule and crosscheck your captain’s availability. We will try our best to accommodate your request.

Captain Wolfgang is on the water with other customers at the moment or is finished for the day. Please leave a message and we’ll be sure to relay your information to him.

Yes, we are open 7 days a week and are hosting voyages 365 days a year. No days off.

Yes, a chilled bottle of wine and barware are included in all sunset tours, along with a light fruit and cheese tray.

GENTLE WAKE NAPLES LLC BOAT TOUR LIABILITY WAIVER AND RELEASE * I understand that participation in a boat tour operated by Gentle Wake Naples, LLC involves inherent risks, including but not limited to slips, falls, rough water, weather conditions, collisions, equipment failure, and interactions with marine life, which may result in injury, property damage, or death. I knowingly and voluntarily assume all such risks.   In consideration of being permitted to participate in the activity, I, for myself, my heirs, personal representatives, and assigns, hereby release, waive, discharge, and covenant not to sue Gentle Wake Naples, LLC, its owners, officers, captains, crew members, agents, employees, representatives, affiliates, and insurers (collectively, “Released Parties”) from any and all liability, claims, demands, actions, causes of action, damages, losses, or expenses of any kind arising out of or related to my participation in the tour, including but not limited to those caused by the negligence of the Released Parties. I affirm that I am physically able to participate and agree to follow all safety instructions provided by the captain and crew. I understand that the vessel has no medical facilities and that emergency response may be delayed. In the event of an emergency, I authorize the Released Parties to secure medical treatment on my behalf and agree that I am responsible for any associated costs. This agreement shall be governed by the laws of the State of Florida. Any dispute related to this agreement shall be resolved exclusively in the appropriate courts of Florida. By signing below, I acknowledge that I have read and understand this waiver and release, and I sign it voluntarily.

Book online at www.thegentlewake.com The booking system is accurate and portrays current availability.

Yes, There is a free parking garage and free street parking onsite. Please refer to the Bayfront Marina Map in your confirmation email.

Smoking is only allowed on the Slow Burn Voyage. However, if a customer books a private cruise on any of the other time slots, they are allowed to smoke. Basically, if you own the entire boat for the timeslot you have the ability to smoke on any of the other themed voyages.

We operate current year 2026 new Hurricane Day Boats. They are 23 feet in length and can accommodate up to 6 passengers and potentially 8.

Kids, infants, seniors are all the same price.

Yes, children under 6 are required to wear lifejackets while underway according to Florida Law. We provide children and infant life jackets.

No, all our voyages are private. We’ve designed them to offer a personalized and exclusive experience, much like a concierge service.

Absolutely, you can do what you please on any of our charters.